The present invention relates to the process of forming alkylated polyamines and, more particularly, to the process of forming fatty polyamines. The subject alkylated polyamines are presently formed by complex synthetic methods such as are described in U.S. Pat. Nos. 3,898,188; 3,899,534; and 4,096,105. The single step catalytic process of the present invention permits the formation of the desired material in an economic manner.
Catalytic aminomethylation of olefins with secondary monoamines, carbon monoxide and hydrogen is well known and was initially taught by Dr. Walter Reppe in Experiention, Vol. 5, p. 93 (1949); German Pat. No. 839,800 (1952) and Liebigs Ann. Chem., Vol. 582, p. 148 (1953). The value of the process was, however, of limited value due to the required use of large quantities of toxic iron or nickel carbonyls as the catalyst, the rapid rate of consumption of the catalyst, the slow rate of reaction, and the poor yields obtained. Moreover, the reaction was taught to be restricted to monoolefins and to low molecular weight monoamines.
Aminomethylation of other monoolefins has been carried out in the presence of other metal carbonyls, but the reactions have been found to be non-selective and produce, at best, only moderate yields of amines. For example, U.S. Pat. Nos. 2,422,631 and 3,234,283 disclose that lower olefins, carbon monoxide, hydrogen, and a secondary monoamine will form, in low yields, tertiary amines in the presence of cobalt hydrocarbonyl or dicobalt octocarbonyl as well as certain other cobalt compounds.
More recently, U.S. Pat. Nos. 3,513,200 and 4,096,150 have disclosed the utilization of Group VIII metal compounds as suitable compounds to catalyze the reaction between monoamines and monomeric olefins with hydrogen and carbon monoxide to form low molecular weight tertiary amines. The above reactions are generally plagued by the formation of significant amounts of byproducts and by the required use of hydrogen which is both unsafe and expensive. The reactions are, therefore, not deemed suitable for the formation of specific compounds.
Alkylated polyamines and products derived therefrom are highly desired compounds known to be useful as surfactants, flocculating agents, softeners and as a desired component of some coating compositions. Conventional methods of forming such alkylated polyamines have been difficult and costly. It is highly desired to find an economical process for forming alkylated polyamines and especially for the formation of fatty amines.